Dichloromethane → HCID 9875552, compound

HRID 1936901Notes

Reaction equation

HRID 1936901 reaction equation
C[Si](I)(C)C.C[O:7][C:8](=[O:54])[C@H:9]([O:23][C:24]1[C:29]([Br:30])=[CH:28][C:27]([C:31]2[CH:36]=[CH:35][C:34]([C:37]3[C:38]4[CH:52]=[CH:51][CH:50]=[CH:49][C:39]=4[S:40][C:41]=3[CH2:42][C:43]3[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=3)=[CH:33][CH:32]=2)=[CH:26][C:25]=1[Br:53])[CH2:10][CH2:11][N:12]1[C:20](=[O:21])[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]1=[O:22].C(Cl)Cl>O>[CH2:42]([C:41]1[S:40][C:39]2[CH:49]=[CH:50][CH:51]=[CH:52][C:38]=2[C:37]=1[C:34]1[CH:33]=[CH:32][C:31]([C:27]2[CH:28]=[C:29]([Br:30])[C:24]([O:23][C@H:9]([CH2:10][CH2:11][N:12]3[C:20](=[O:21])[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13]3=[O:22])[C:8]([OH:54])=[O:7])=[C:25]([Br:53])[CH:26]=2)=[CH:36][CH:35]=1)[C:43]1[CH:48]=[CH:47][CH:46]=[CH:45][CH:44]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 85247Trimethylsilyl iodide2×HCID 54440153HCID 54440153, compound

Product 1

HCID 9875552HCID 9875552, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

Trimethylsilyl iodide (0.29 mL, 2.07 mmol) was added into a mixture of (2R)-2-[4′-(2-benzyl-benzo[b]-thiophen-3-yl)-3,5-dibromo-biphenyl-4-yloxy]-4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-butyric acid methyl ester (1.1 g, 1.38 mmol), and methylene chloride (10 mL). The reaction mixture was stirred at 50° C. for 24 hours. An additional 0.29 mL of trimethylsilyl iodide was added and the mixture was stirred for 48 hours, poured into water and extracted with ethyl acetate. The organic extracts were washed with aqueous sodium bisulfite and dried over MgSO4. Evaporation and purification by flash chromatography on silica gel (hexanes/EtAOc 2:1) gave white solid (0.92 g, 94% yield): mp 113-115° C.; MS m/e 778 (M−H)+;

Workup

  1. stirringthe mixture was stirred for 48 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with aqueous sodium bisulfite
  4. dry with materialdried over MgSO4
  5. customEvaporation and purification by flash chromatography on silica gel (hexanes/EtAOc 2:1)

Sources & evidence

ORD record
ord-890d062a19cd49309251cfa14f3102ec
Source dataset
uspto-grants-2002_05
Patent number
US06391897B2

Reaction notes

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